Worst Trades in Yankees History

Worst Trades in Yankees History No. 2 –

Adam: Why is Vazquez number two? Well, it is because the Bombers did it twice. The Yankees signed Vazquez to an extension after acquiring him from Montreal, a four-year deal worth over $40 Mil. At face value, the deal seemed good and Vazquez was only 27 years old. At the time of the signing, he was considered one of the better pitchers in baseball. He rewarded the Yankees with a 4.91 ERA, 100 fewer strikeouts than the previous season, and an absolute implosion against the hated Red Sox. In game 7 of the horrific 2004 ALCS, he pitched two innings giving up five walks and three runs. The Yankees were able to trade away the final three years of the contract and get away. So why is he on the list?

Well, the Yankees did not learn. A few years later, after a stellar season in Atlanta where he struck out 238 with a 2.87 ERA, the Yankees brought him back to New York yet again. Well, this time he would raise his ERA to 5.32 and again strike out more than 100 batters less than the year before. He was a bad addition not once but twice and that is how he makes it into number two on my list of worst trades in Yankees history.

Rich:  The second worst trade in Yankees history has to be when they traded a prospect named Willie McGee to the Cardinals for a pitcher named Bob Sykes.  Willie McGee won the Rookie of the Year for the Cardinals, an MVP award, and helped the Cardinals win the World Series.  Bob Sykes, well, there is a reason you probably don’t know who he is – he never even pitched for the Yankees.  Dealing prospects is always tough because you just never know what will happen, and McGee is the perfect example of that.


Worst Trades in Yankees History No. 1 –

Rich: My choice for the worst trade in Yankees history is the trade of Jay Buhner to the Mariners for Ken Phelps.  In the 1980s, George Steinbrenner was on a power kick and always seemed to want the guy with the best power, no matter what else they did at the plate – this was Ken Phelps.  Jay Buhner was a prospect that was expendable.  Buhner ended up with Seattle in the trade and hit 310 HRs over a 15-year career.  Phelps over two seasons with the Yankees hit 17 HRs and batted .240.  Granted, if we kept Buhner, we never would have got Paul O’Neill a couple of years later, but this trade was so lopsided against the Yankees, it has to be the worst trade they’ve ever made (it was even mentioned in several episodes of Seinfeld due to how bad this trade was and how us fans of the Yankees in the 1980s felt about it).


Adam: The worst trade in the storied history of the New York Yankees has to be when the Bombers shipped Willie McGee to the St Louis Cardinals for pitcher Bob Sykes. I cannot even come up with a way when the deal ever made sense for Yankees, including the day of the deal. Let’s just make this worse shall we? Sykes never pitchers for the Yankees and the year of the trade was his last year in professional baseball. While McGee went on to win the 1982 Rookie of the Year, the 1985 Most Valuable Player Award, three Gold Gloves, four All-Star appearances, and the 1985 World Series. He was also part of three other World Series teams. So I guess you can say the deal did not exactly end even and that is how he makes it into number one on my list of worst trades in Yankees history.


Worst Trades in Yankees History Final Thoughts

Adam: Dealing away or trading for prospects is always tricky. Heck, even making a call on a veteran is not an exact since. Sometimes it works (Ruth, Maris etc.) and other times it falls flat on its face (see this list). In all honesty, if these are the worst trades the organization has attempted then the 100+ years have not been that bad. It is still frustrating to see a deal that gets you absolutely nothing ever. Overall, it is an exercise in hope every time a deal is inked. You win some and you lose some. You can just hope the wins are worth it in the long run.

Rich:  Trades can be a mixed bag.  You just never know what will happen and who will get the better end of the deal.  Sometimes you get a player that helps you win a title, others you deal away a player that ends up winning for someone else.  If you deal prospects, it is even more of an unknown.  Sometimes a trade with prospects has to be made because the prospect simply has no place in the organization going forward (McGriff and Mattingly for instance) and it ends up being a very bad deal.  When doing trades, you simply hope you get something good out of the deal, but sadly, as we discussed, there are many times where that is not the case.

Now you know our Top-5 worst trades in Yankees history. Here at NY Yankees Digest we are all for readers commenting but can we make a suggestion? Why don’t you write your own piece? It can be 3000 words or even 300.  Here we encourage different opinions and want to give you a chance to build your brand. Join us and let your voice be heard. Just check out the Write With Us link to get started. Don’t worry its easy and remember you can build your brand by writing with us and not for us. That is a big difference. It is all about you in your words.

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